Color filter having novel dyestuff

ABSTRACT

Dyestuffs represented by the below-described formula (1), that is, dyestuffs formed of a chromophoric nucleus and a bisphenol introduced therein have excellent solubility in solvents and binder resins, and can provide color filters having excellent transmittance characteristics and durability. ##STR1## wherein Dye represents a chromophoric nucleus, X represents a direct bond or a divalent connecting group, R 1  to R 10  and n are defined with the provision that one of R 9  and R 10  has 3 or more carbon atoms.

This application is a continuation of application Ser. No. 08/269,771,filed Jul. 1, 1994, now abandoned.

BACKGROUND OF THE INVENTION

a) Field of the Invention

This invention relates to dyestuffs, which play an important role incolor filters for display devices such as liquid crystal television setsand also in color separation filters for image pickup tubes, colorcopiers, video printers and the like.

b) Description of the Related Art

Conventionally known dyestuffs for filters include, as blue dyestuffs,anthraquinone dyestuffs (Japanese Patent Laid-Open Nos. 136604/1987 and197459/1987) and triphenylmethane dyestuffs ("1990s Development andMarket Trend of Special Functional Dyestuffs", 47-48, CMC Co., Ltd.); asred dyestuffs, anthraquinone dyestuffs (Japanese Patent Laid-Open No.74960/1987), azo dyestuffs ("1990s Development and Market Trend ofSpecial Functional Dyestuffs", 47, CMC Co., Ltd.) and perinone dyestuffs(Japanese Patent Laid-Open No. 136606/1987); as green dyestuffs,anthraquinone dyestuffs (Japanese Patent Laid-Open No. 246258/1986),triphenylmethane dyestuffs ("1990s Development and Market Trend ofSpecial Functional Dyestuffs", 47-48, CMC Co., Ltd.), phthalocyaninedyestuffs (Japanese Patent Laid-Open Nos. 249102/1985, 140902/1986,254903/1986, 254904/1986, 6904/1989, 88505/1989, and 233401/1989),perinone dyestuffs (Japanese Patent Laid-Open No. 136606/1987), andnaphthoquinone dyestuffs (Japanese Patent Laid-Open No. 268761/1986);and as yellow dyestuffs, azo and vat-dye pigments ("1990s Developmentand Market Trend of Special Functional Dyestuffs", 48, CMC Co., Ltd.)and water-soluble azo dyes (Japanese Patent Laid-Open Nos. 204010/1984and 204011/1984).

As to the blue dyestuffs, the anthraquinone compounds do not permitsufficient light transmission around 440 nm but have high transmittanceat wavelengths of 500 nm and longer, so that they have a broadtransmittance curve. In the case of the triphenylmethane dyestuffs,their molecules are in an ionized form so that they are suited forcoloring filters making use of gelatin or casein as a substrate and werehence used in gelatin-type filters. Those filters themselves however hadlow light fastness and heat resistance. Turning next to the reddyestuffs, the anthraquinone compounds and perinone compounds areaccompanied by the drawback that they have low transmittance and poorcolor visibility, although their durability is good. The azo compoundsare water-soluble and are thus suited for coloring filters making use ofgelatin or casein as a substrate. The azo compounds were thereforeemployed in gelatin-type filters. Due to poor heat and moistureresistance of the filters themselves, their applications were limited.Further, for poor light fastness, heat resistance and moistureresistance of the dyestuffs themselves, the filters were not usable ingeneral devices. Among the green dyestuffs, sulfo-containingphthalocyanine compounds which are water-soluble compounds are suited incoloring filters making use of gelatin or casein as a substrate and werehence used in gelatin-type filters. Their applications were howeverlimited due to poor heat and moisture resistance of the filtersthemselves. Further, the anthraquinone and naphthoquinone dyestuffs donot permit sufficient transmission for light of 500-600 nm and theirlight fastness is not sufficient. In the case of the triphenylmethanedyestuffs, their molecules are in an ionized form so that they aresuited for coloring filters making use of gelatin or casein as asubstrate and were hence used in gelatin-type filters. Those filtersthemselves however had poor heat and moisture resistance so that alimitation was imposed on their applications. In addition, due to poorlight fastness, heat resistance and moisture resistance of the dyestuffsthemselves, they were not usable in general display devices. Dealingfinally with the yellow dyestuffs, the azo pigments and vat dyes areused for the fabrication of filters by the pigment dispersion method.Although filters obtained by the pigment dispersion method have highpattern accuracy and excellent heat resistance and light fastness, theyare accompanied by the following drawbacks:

(1) Due to scattering of light by pigment particles, the filters haveinferior light transmittance and poor contrast.

(2) Prior to coating a photosensitive resin in which a pigment isuniformly dispersed, it is necessary to eliminate dirt and largeparticles by causing the photosensitive resin to pass through a screen,leading to potential problems, for example, troubles in the fabricationprocess such as screen clogging due to agglomeration of pigmentparticles.

The water-soluble azo dyes are used for the fabrication of filters bythe dyeing method. Color filters obtained by the dyeing method areexcellent in pattern resolution, dimensional accuracy and lighttransmission and also high in color lightness. They are howeveraccompanied with the drawback that their heat resistance is insufficientfor their use of gelatin or casein as a photosensitive resin.

SUMMARY OF THE INVENTION

An object of the present invention is to improve the above-describeddrawbacks of the conventional filters and dyestuffs and hence to obtaina filter excellent in transmittance characteristics, light fastness andheat resistance.

To attain the above-described object, the present inventors haveproceeded with an extensive investigation. As a result, it has beenfound that introduction of a specific substituent group, namely, a grouprepresented by the below-described formula (7) into a chromophoricnucleus can provide a dyestuff having a solubility of 3% or higher in asolvent such as Ethyl Cellosolve acetate or Butyl Cellosolve acetate anda solubility of 10% or higher in a binder polymer and thus a filterexcellent in transmittance characteristics and durability and free oflight scattering, leading to the completion of the present invention. Asa reason for the excellent solubility of the dyestuff having thespecific substituent group represented by formula (7) in the solvent andbinder polymer, it has been found that the existence of the phenolichydroxyl group and one or more alkyl groups in R⁹ and R¹⁰ iscontributory and when one of R⁹ and R¹⁰ has 3 or more carbon atoms, goodsolubility is shown. ##STR2## wherein R¹ to R¹⁰ have the same meaningsas in formula (1). Incidentally, the term "dissolved" as used hereinmeans that a dyestuff is present in the form of single molecules of 0.01μm or smaller in diameter.

The present invention therefore relates to a novel dyestuff representedby the following formula (1) and also to its use.

Formula (1) being: ##STR3## wherein Dye represents a chromophoricnucleus, X represents a direct bond or a divalent connecting group, R¹to R⁸ independently represent a hydrogen atom, a halogen atom, asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedcycloalkyl group or a substituted or unsubstituted alkoxyl group, R⁹ andR¹⁰ independently represent a hydrogen atom or a substituted orunsubstituted alkyl group, and n stands for an integer of 1 to 10, withthe proviso that the total carbon number of R⁹ and R¹⁰ is at least 3.

The dyestuff according to the present invention, which has been obtainedby introducing the substituent represented by formula (7) into achromophoric nucleus, has excellent solubility in solvents and binderresins and has made it possible to provide color filters excellent intransmittance characteristics and durability.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates steps for the formation of a stripe filter;

FIG. 2 diagrammatically shows transmittance characteristics of a filterobtained in Example 1;

FIG. 3 diagrammatically depicts transmittance characteristics of afilter obtained in Example 2;

FIG. 4 diagrammatically illustrates transmittance characteristics of afilter obtained in Example 3;

FIG. 5 diagrammatically presents transmittance characteristics of afilter obtained in Comparative Example 1;

FIG. 6 diagrammatically shows transmittance characteristics of a filterobtained in Comparative Example 2;

FIG. 7 diagrammatically depicts transmittance characteristics of afilter obtained in Example 5;

FIG. 8 diagrammatically illustrates transmittance characteristics of afilter obtained in Example 6;

FIG. 9 diagrammatically presents transmittance characteristics of afilter obtained in Comparative Example 3;

FIG. 10 diagrammatically shows transmittance characteristics of a filterobtained in Example 7; and

FIG. 11 diagrammatically depicts transmittance characteristics of afilter obtained in Example 8.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

The novel dyestuff according to the present invention is represented byformula (1), namely, is a novel compound containing a group or groupsrepresented by formula (7) described above. A description willhereinafter be made of the substituents represented R¹ to R¹⁰ in formula(1).

Examples of the unsubstituted alkyl group can include linear or branchedalkyl groups having 1 to 20 carbon atoms, preferably linear or branchedalkyl groups having 1 to 12 carbon atoms, and more preferably, linear orbranched alkyl groups such as methyl, ethyl, n-propyl, iso-propyl,n-butyl, iso-butyl, sec-butyl, t-butyl, n-pentyl, iso-pentyl,neo-pentyl, 1,2-dimethylpropyl, n-hexyl, n-dodecyl, 2-methylbutyl,2-methylpentyl, 1,3-dimethylbutyl, 1-iso-propylpropyl,1,2-dimethylbutyl, n-heptyl, 1,4-dimethylpentyl,2-methyl-1-iso-propylpropyl, 1-ethyl-3-methylbutyl, n-octyl,2-ethylhexyl, 3-methyl-1-iso-propylbutyl,2,2-dimethyl-1-iso-propyl-1-t-butylpropyl and n-nonyl.

Illustrative of the substituted alkyl group are linear or branched alkylgroups substituted by one or more of alkoxy, halogen, hydroxyl and/oramino substituents and having 1 to 30 carbon atoms, preferably linear orbranched alkyl groups substituted by one or more of alkoxy, halogen,hydroxyl and amino substituents and having 1 to 8 carbon atoms, and morepreferably alkoxyalkyl groups such as methoxymethyl, methoxyethyl,ethoxyethyl, propoxyethyl, butoxyethyl, γ-methoxypropyl, γ-ethoxypropyl,methoxyethoxyethyl, ethoxyethoxyethyl, dimethoxymethyl, diethoxymethyl,dimethoxyethyl and diethoxyethyl, halogenated alkyl groups such aschloromethyl, 2,2,2-trichloroethyl, trifluoromethyl and1,1,1,3,3,3-hexafluoro-2-propyl, hydroxyalkyl groups such ashydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyland hydroxyoctyl, and aminoalkyl groups such as2-N,N-dimethylaminoethyl, 2-N,N-diethylaminoethyl and3-N,N-diethylaminopropyl.

Examples of the unsubstituted alkoxy groups can include linear orbranched alkoxy groups having 1 to 10 carbon atoms, preferably linearalkoxyl groups having 1 to 5 carbon atoms, more preferably methoxy,ethoxy, propoxy, butoxy and pentyloxy groups. Examples of thesubstituted alkoxy group can include linear or branched alkoxy groupssubstituted by one or more alkoxy and/or halogen substituents and having1 to 20 carbon atoms, preferably linear alkoxy groups substituted by oneor more alkoxy and/or halogen substituents and having 1 to 8 carbonatoms, more preferably alkoxyalkoxy groups such as methoxymethoxy,methoxyethoxy, ethoxyethoxy, ethoxymethoxy, methoxybutoxy, ethoxybutoxyand butoxybutoxy, and methoxy, ethoxy, propoxy, butoxy and pentyloxygroups substituted by one or more halogen atoms such as chlorine,bromine, iodine and/or fluorine.

Illustrative of the unsubstituted cycloalkyl group can includecycloalkyl groups having 5 to 12 carbon atoms. Preferred examples caninclude cyclopentyl, cyclohexyl and cycloheptyl groups. Examples of thesubstituted cycloalkyl group can include cycloalkyl groups substitutedby one or more alkyl, halogen and/or alkoxy substituents and having 1 to20 carbon atoms. Preferred examples can include cyclopentyl, cyclohexyland cycloheptyl groups substituted by one or more of alkyl groups suchas methyl, ethyl, propyl and butyl, halogen atoms such as chlorine,bromine, iodine and fluorine and alkoxy groups such as methoxy, ethoxy,propoxy and butoxy. Illustrative of the unsubstituted aryl group caninclude aryl groups having 6 to 20 carbon atoms, preferably phenyl andnaphthyl groups. Illustrative of the substituted aryl group can includearyl groups substituted by one or more alkyl, halogen and/or alkoxysubstituents and having 6 to 30 carbon atoms, preferably phenyl andnaphthyl groups substituted by one or more of linear or branched alkylgroups such as methyl, ethyl, propyl, i-propyl, butyl and t-butyl,halogen atoms such as chlorine, bromine, fluorine and iodine and alkoxygroups such as methoxy, ethoxy, propoxy and butoxy. Illustrative halogenatoms include chlorine, bromine, iodine and fluorine atoms.

The chromophoric nucleus represented by Dye can be any one of knownnuclei described in literature, such as azo, anthraquinone,phthalocyanine, quinophthalone, cyanine, dicyanostyryl, tricyanovinyl,indoaniline, fused polycyclic and indigo chromophoric nucleiillustrative literature include "SHIKISO HANDBOOK (Dyestuff Handbook)",compiled by Okawara et al., Kodansha, Ltd. (1986) and "THE CHEMISTRY OFSYNTHETIC DYES", Vol. 1 to Vol. 6, Edited by K. Venkataraman, AcademicPress Inc.!

Their skeletons are specifically listed below. ##STR4##

Preferred chromophoric nuclei can include:

anthraquinone derivatives--for example, 1,4-bis(anilino)anthraquinone,1,4-bis(4-ethyl-2,6-dimethylanilino)anthraquinone,1,4-bis(6-bromo-2,4-dimethylanilino)anthraquinone,1,4-bis(anilino)-5,8-dihydroxyanthraquinone,1,5-diamino-4,8-dihydroxyanthraquinone,1-toluylamino-4-hydroxyanthraquinone,1,4-diamino-2-phenylthioanthraquinone,1-amino-2-phenoxy-4-hydroxyanthraquinone, and1-amino-4-anilino2-phenylthioanthraquinone;

quinophthalone derivatives--for example, C.I. Disperse Yellow 54, andC.I. Disperse Yellow 64;

azo derivatives--for example, diphenylazo compounds, thiazole-phenylazocompounds, isothiazolephenylazo compounds, thiophene-phenylazocompounds, pyridine-phenylazo compounds, imidazole-phenylazo compounds,pyridone-phenylazo compounds, pyrazolonephenylazo compounds,benzothiazole-phenylazo compounds, and benzoisothiazole-phenylazocompounds; and

phthalocyanine compounds--for example, α-alkoxyphthalocyanines.

The above chromophoric nuclei can contain one to eight of the followingsubstituent groups:

linear or branched alkyl groups such as methyl, ethyl, n-propyl,iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, n-pentyl,iso-pentyl, neo-pentyl, 1,2-dimethylpropyl, n-hexyl, n-dodecyl,2-methylbutyl, 2-methylpentyl, 1,3-dimethylbutyl, 1-iso-propylpropyl,1,2-dimethylbutyl, n-heptyl, 1,4-dimethylpentyl,2-methyl-1-iso-propylpropyl, 1-ethyl-3-methylbutyl, n-octyl,2-ethylhexyl, 2-methyl-1-iso-propylbutyl,2,2-dimethyl-1-iso-propyl-1-t-butylpropyl, and n-nonyl;

alkoxyalkyl groups such as methoxymethyl, methoxyethyl, ethoxyethyl,propoxyethyl, butoxyethyl, γ-methoxypropyl, γ-ethoxypropyl,methoxyethoxyethyl, ethoxyethoxyethyl, dimethoxymethyl, diethoxymethyl,dimethoxyethyl, and diethoxyethyl;

halogenated alkyl groups such as chloromethyl, 2,2,2-trichloroethyl,trifluoromethyl, 1,1,1,3,3,3-hexafluoro-2-propyl;

hydroxyalkyl groups such as hydroxymethyl, hydroxyethyl, hydroxypropyl,hydroxybutyl, hydroxypentyl, and hydroxyoctyl;

aryl groups such as phenyl, naphthyl and indenyl;

substituted aryl groups such as phenyl, naphthyl and indenyl groupshaving one or more of linear or branched alkyl groups such as methyl,ethyl, propyl, iso-propyl, butyl, 2-methylpropyl, pentyl and neo-pentyl,alkoxy groups such as methoxy, ethoxy and propoxy, and halogen atomssuch as chlorine, fluorine, bromine and iodine;

aryloxy groups such as phenoxy and naphthyloxy;

substituted aryloxy groups such as phenoxyl and naphthyloxy groupshaving one or more of linear or branched alkyl groups such as methyl,ethyl, propyl, iso-propyl, butyl, 2-methylpropyl, pentyl and neo-pentyl,alkoxy groups such as methoxy, ethoxy and propoxy, and halogen atomssuch as chlorine, fluorine, bromine and iodine;

arylthio groups such as phenylthio and naphthylthio;

substituted arylthio groups such as phenylthio and naphthylthio groupshaving one or more of linear or branched alkyl groups such as methyl,ethyl, propyl, iso-propyl, butyl, 2-methylpropyl, pentyl and neo-pentyl,alkoxy groups such as methoxy, ethoxy and propoxy, and halogen atomssuch as chlorine, fluorine, bromine and iodine;

arylamino groups such as phenylamino and naphthylamino;

substituted arylamino groups such as phenylamino and naphthylaminogroups having one or more of linear or branched alkyl groups such asmethyl, ethyl, propyl, iso-propyl, butyl, 2-methylpropyl, pentyl andneo-pentyl, alkoxy groups such as methoxy, ethoxy and propoxy, andhalogen atoms such as chlorine, fluorine, bromine and iodine;

linear or branched alkylamino groups such as methylamino, ethylamino,n-propylamino, iso-propylamino, n-butylamino, iso-butylamino,sec-butylamino, t-butylamino, n-pentylamino, isopentylamino,neo-pentylamino, 1,2-dimethylpropylamino, n-hexylamino, n-dodecylamino,2-methylbutylamino, 2-methylpentylamino, 1,3-dimethylbutylamino,1-iso-propylpropylamino, 1,2-dimethylbutylamino, n-heptylamino,1,4-dimethylpentylamino, 2-methyl-1-iso-propylpropylamino,1-ethyl-3-methylbutylamino, n-octylamino, 2-ethylhexylamino,2methyl-1-iso-propylbutylamino,2,2-dimethyl-1-iso-propyl-1-t-butylpropylamino, and n-nonylamino;

linear or branched dialkylamino groups such as dimethylamino,diethylamino, di(n-propyl)amino, di(iso-propyl)amino, di(n-butyl)amino,di(iso-butyl)amino, di(sec-butyl)amino, di(t-butyl)amino,di(n-pentyl)amino, di(iso-pentyl)amino, di(neo-pentyl)amino,di(1,2-dimethylpropyl)amino, di(n-hexyl)amino, di(n-dodecyl)amino,di(2-methylbutyl)amino, di(2-methylpentyl)amino,di(1,3-dimethylbutyl)amino, di(1-iso-propylpropyl)amino,di(1,2-dimethylbutyl)amino, di(n-heptyl)amino,di(1,4-dimethylpentyl)amino, di(2-methyl-1-iso-propylpropyl)amino,di(1-ethyl-3-methylbutyl)amino, di(n-octyl)amino, di(2-ethylhexyl)amino,di(2-methyl-1-iso-propylbutyl)amino,di(2,2-dimethyl-1-iso-propyl-1-t-butylpropyl)amino, anddi(n-nonyl)amino; and

amino group; hydroxyl group, nitro group; cyano group; and halogen atomssuch as chlorine, bromine, iodine and fluorine.

Particularly preferred, illustrative chromophoric nuclei can include,from the standpoint of durability, dyestuff skeletons represented by thefollowing formulas (2), (5) and (6):

Formula (2) being: ##STR5## wherein R¹ to R¹⁰ have the same meanings asdefined in formula (1); R¹¹ and R¹² independently represent a hydrogenatom, an unsubstituted, linear or branched alkyl group having 1 to 20carbon atoms, or a linear or branched alkyl group substituted by one ormore halogen, alkoxy, hydroxyl and/or amino groups and having 1 to 30carbon atoms in total; and Y represents a hydroxyl group, an aminogroup, a substituted or unsubstituted monoalkylamino group, or asubstituted or unsubstituted arylamino group.

Formula (5) being: ##STR6## wherein R¹ to R¹⁰ have the same meanings asdefined in formula (1); R¹⁴ and R¹⁵ independently represent a hydrogenatom, an unsubstituted, linear or branched alkyl group having 1 to 20carbon atoms, a linear or branched alkyl group substituted by one ormore halogen, alkoxy, hydroxyl and/or amino groups and having 1 to 30carbon atoms in total, an unsubstituted, linear or branched alkoxy grouphaving 1 to 20 carbon atoms, a linear or branched alkoxy groupsubstituted by one or more halogen, alkoxy, hydroxyl and/or amino groupsand having 1 to 20 carbon atoms in total, or a halogen atom; R¹⁶represents a hydrogen atom or a halogen atom; and X represents --CO--,--COOCH₂ CO-- or --COOCH₂ CH₂ CO--.

Formula (6) being: ##STR7## wherein R¹ to R¹⁰ have the same meanings asdefined in formula (1); R¹⁷ represents an unsubstituted, linear orbranched alkyl group having 1 to 20 carbon atoms or a linear or branchedalkyl group substituted by one or more halogen, alkoxy, hydroxyl and/oramino-groups and having 1 to 30 carbon atoms in total; and X represents--CO-- or --COOCH₂ CO--.

Where X represents a divalent connecting group in formula (1), noparticular limitation is imposed on the divalent connecting group andany divalent connecting group can be used. Preferred examples of thedivalent connecting group include alkylene groups such as methylene,ethylene, methylethylene, 1,2-dimethylethylene, propylene, butylene,methoxymethylethylene and hexylene; diesters such as --COOCH₂ CO--,--COOCH₂ CH₂ CO--, --COOCH₂ CH₂ CH₂ CO--, --COOCH(CH₃)CH₂ CO-- and--COOCH₂ CH(CH₃)CO--; --NHCO--; and --CO--.

As a process for the synthesis of the dyestuff represented by formula(1), a compound represented by the below-described formula (8) andanother compound represented by the below-described formula (9) arereacted, for example, under heat at 50-°200° C. for about 0.5-20 hoursin the presence of a base such as potassium carbonate, sodium carbonate,sodium hydroxide, potassium hydroxide, sodium acetate or potassiumacetate either in a solventless manner or in a solvent, for example, anaromatic hydrocarbon such as benzene, toluene or xylene, a halogenatedhydrocarbon such as chlorobenzene or dichlorobenzene, asulfur-containing solvent such as sulfolane or dimethylsulfoxide, anamide solvent such as dimethylformamide or dimethylacetamide, aCellosolve solvent such as Ethyl Cellosolve, Methyl Cellosolve or ButylCellosolve, 1,3-dimethyl-2-imidazolidinone, or N-methylpyrrolidone.

Formula (8) being:

    Dye-Br                                                     (8)

wherein Dye represents a chromophoric nucleus.

Formula (9) being: ##STR8## wherein R¹ to R¹⁰ have the same meaning asdefined in the formula (1).

The term "resin composition" as used herein means a photoresistcomposition which is used upon fabrication of color filters for LCDs orcolor separation filters for image pickup tubes. The photoresistcomposition is formed of (1) a dyestuff, (2) a binder polymer, (3) aphotopolymerizable polyfunctional monomer, (4) a photopolymerizationinitiator, and (5) other additives. The photoresist composition can bediluted with a solvent, for example, an acetate such as ethyl cellosolveacetate, methyl cellosolve acetate, butyl cellosolve acetate, butylcellosolve acetate or propylene glycol monomethyl ether acetate, alactate ester such as ethyl lactate, methyl lactate, propyl lactate orbutyl lactate, a pylvate ester such as ethyl pylvate, methyl pylvate,propyl pylvate or butyl pylvate, a ketone such as methyl-2-n-amylketone, methyl ethyl ketone or cyclohexanone, or an ester such as butylacetate, ethyl acetate, methyl acetate, propyl acetate or methyl3-methoxypropionate.

(1) The dyestuff can be used in an amount of 1-100 parts, preferably10-40 parts per 100 parts of the binder polymer. Two or more dyestuffsaccording to the present invention can be used in combination. It isalso possible to additionally incorporate one or more color-adjustingdyestuffs.

(2) The binder polymer is to impart film-forming ability to thephotoresist. An alkali-developable binder polymer contains acid groups(carboxyl groups) and can be dissolved in an alkali developer. Examplesof such binder polymers can include various copolymers containing methylmethacrylate as a principal component, polystyrene, acrylonitrile,(meth)acrylic acids and the like.

(3) The photopolymerizable polyfunctional monomer undergoes radicalpolymerization in the presence of a photoinitiator and tangles thebinder polymer to cross-link and cure the same, whereby the binderpolymer is rendered insoluble in the developer. The photo-polymerizablepolyfunctional monomer can be used in an amount of 1-100 parts,preferably 10-50 parts per 100 parts of the binder polymer. Examples ofsuch monomers can include polyfunctional (meth)acrylates such astrimethylolpropane triacrylate, polyethylene glycol di(meth)acrylates,polyalkylene glycol di(meth)acrylates and (di)pentaerythritol (tri tohexa)acrylates as well as polyfunctional (meth)acrylates of the epoxy,urethane, ester, ether, bisphenol and spiran types.

(4) The photopolymerization initiator, upon exposure to ultravioletrays, generates active radicals as an initiator or sensitizer andinduces radical polymerization of a polyfunctional monomer containingpolymerizable groups such as (meth)acryloyl groups. Thephotopolymerization initiator can be used in an amount of 0.01-100parts, preferably 1-20 parts per 100 parts of the binder resin. Examplesof such photopolymerization initiators include intermolecular hydrogenabstraction type photopolymerization initiators, such as those of thebenzophenone, thioxanthone and anthraquinone type, and intramolecularlinkage cleaving type photopolymerization initiators such as those ofthe acetophenone and benzoin ether types.

(5) Other additives include polymerization inhibitors such as those ofthe hydroquinone and bisphenol types.

From dyestuffs according to this invention, a color filter for an LCD ora color separation filter for an image pickup tube can be fabricated,for example, by casting or spin-coating a photosensitive resin orphotopolymerizable monomer in the form of film on a substrate, exposingthe film to light to pattern the same and then dyeing the resin layerwith the dyestuff by dipping or a like method, by vacuum-depositing adyestuff layer and patterning it in accordance with dry etching orlifting-off, by dissolving or dispersing the dyestuff beforehand in aresist composition or, forming the resulting solution or dispersion intoa film on a substrate in accordance with casting, spin-coating or thelike and then exposing the film to light to pattern the same, or bypatterning the dyestuff on a substrate in accordance with a printingprocess.

Such patterning of a dyestuff layer as described above can be conductedon an optically transparent substrate. No particular limitation isimposed on the substrate to be used, insofar as the substrate permitspatterning of a dyestuff layer and the color filter so formed haspredetermined function.

Illustrative usable substrates can include glass plates; and resin filmsand plates made of polyvinyl alcohol, hydroxyethylcellulose, polymethylmethacrylate, polyesters, polybutyral, polyamides, polyethylene,polyvinyl chloride, polyvinylidene chloride, polycarbonates, copolymerscontaining polyolefins, polyvinyl chloride, polyvinylidene chloride orpolystyrene. A patterned dyestuff layer can also be formed integrallywith a substrate which is applicable as a color filter. Examples of thissubstrate can include the luminescent screen of a cathode-ray tube, thelight receiving surface of an image pickup tube, a wafer withsolid-state image pickup elements formed thereon, a contact image sensormaking use of a thin film semiconductor, a display surface for LCD and aphotoconductor for color electrophotography.

Taking the formation of a stripe filter as an example, a typical processfor the formation of a filter will hereinafter be described withreference to FIG. 1.

As is shown at (B) in FIG. 1, a resin composition which has been formedby dissolving or dispersing 1-20 parts of a dyestuff of this inventionin 100 parts of a solution obtained by diluting 20 parts of aphotoresist composition with 80 parts of a solvent is first spin-coatedby a spinner on a glass substrate 1 (A) in FIG. 1! on which a blackmatrix 2 has been formed in advance. Although the thickness of a resistlayer 3 is determined depending on the desired spectral characteristic,it is generally 0.5-100 μm, preferably 1-2 μm. After the coating, theresist layer is pre-baked under adequate temperature conditions (step1). Through a photomask 4 having a predetermined pattern shapecorresponding to a pattern to be formed (stripe pattern), the pre-bakedresist layer is exposed to light or electron beams (ultraviolet rays inthe drawing) to which the resist is sensitive (C) in FIG. 1, step 2!.The resist layer so exposed is then developed to form a colored pattern5 (D) in FIG. 1!. It is also possible to apply, as needed, pretreatmentbefore the development to reduce distortion of the resist layer orrinsing treatment after the development to suppress expansion of theresultant film. Finally, post-baking is conducted under suitableconditions (step 3).

To form a color filter having two or more colors, a serial procedure ofsteps (1) to (3) is repeated as many as needed depending on the numberof the colors employed for the filter while separately using dyestuffscorresponding to the respective colors. This makes it possible toprovide the color filter with the multiple colors. As is illustrated at(E) in FIG. 1, colored patterns 5,6,7 corresponding to three colorsR,G,B, respectively, are formed. To form a black matrix, it is desiredto form the black matrix before the individual dyestuff layers areformed.

From dyestuffs according to this invention, a color filter for use in acolor copying machine or the like can be fabricated, for example, bymixing 0.1-10 parts of the dyestuff of this invention with 100 parts ofa thermoplastic resin, for example, polystyrene, polymethylmethacrylate, a polycarbonate, a polyester, polyvinyl chloride, apolyacetal, a polyphenylene oxide, a polybutylene terephthalate, apolyethylene terephthalate, a vinyl alcohol copolymer, a polysulfone, apolyphenylene sulfide, a polyamide imide, a polyether imide or apolyetheretherketone and forming the resultant colored resin inaccordance with injection molding, stretching or the like, by dissolvingthe dyestuff of this invention either singly or together with a binderin a solvent and forming the solution into a film on a substrate inaccordance with casting, spin-coating or vacuum deposition, or by mixingthe dyestuff with a varnish containing a polyimide resin intermediateand then heating the resulting mixture to form the intermediate into aresin.

Any optically transparent material can be used as the substrate.Illustrative materials include glass; and transparent resins, forexample, polyacrylic resin, polyethylene resin, polyvinyl chlorideresin, polyvinylidene chloride resin, polycarbonate resins, polyethyleneresin, copolymers containing polyolefins, polyvinyl chloride,polyvinylidene chloride or polystyrene.

The present invention will hereinafter be described in detail by thefollowing examples. It is however to be noted that embodiments for thepractice of the present invention are by no means limited to or by thefollowing examples.

EXAMPLE 1

Ten parts of 1-amino-2,4-dibromoanthraquinone, 50 parts of m-toluidineand 11.8 parts of sodium acetate were reacted at 130° C. for 5 hours.The reaction mixture was poured into 1000 parts of 50% aqueous methanolsolution, whereby 9.5 parts of the following compound (10) wereobtained. ##STR9##

After 18.4 parts of 4,4'-butylidenebis(6-t-butyl-m-cresol), 7.2 parts ofpotassium carbonate and 100 parts of sulfolane were stirred at 100° C.for 30 minutes, 9 parts of the compound (10) were added, followed by areaction at 120° C. for 4 hours. The reaction mixture was poured into1000 parts of 50% aqueous methanol solution, and a precipitated solidwas collected by filtration and then dried. By column chromatographicpurification, 7 parts of the following compound (11) were obtained.##STR10##

Melting point: 136-°164° C.

Visible light absorption, λ_(max) : 600 nm εg: 2.0×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₇ H₅₂ N₂ O₄ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            79.66        7.34   3.96                                          Found (%)   79.56        7.46   3.95                                          ______________________________________                                    

One gram of the anthraquinone compound (11) was dissolved in 10 g of aprepolymer ("SD-17", trade name; product of Dainippon Ink & Chemicals,Incorporated). Using a spinner, the resulting solution was spin-coatedon a glass substrate. The resulting film was dried, pre-baked at85-°100° C. for 2-5 minutes and through a mask having a stripe-shapedpattern, exposed to light from a high-pressure mercury lamp (20-30mj/cm², 2 minutes). The film so exposed was then developed to form apattern. Finally, the film so patterned was post-baked at 200°-230° C.for 10-30 minutes so that a blue stripe filter was obtained. Thethickness of the dyestuff layer was 2.1 μm.

The filter had good durability and transmittance characteristics. Itstransmittance characteristics are shown in FIG. 2.

EXAMPLE 2

Ten parts of 1-amino-2,4-dibromoanthraquinone, 50 parts ofcyclohexylamine and 11.8 parts of sodium acetate were reacted at 130° C.for 5 hours. The reaction mixture was poured into 1000 parts of 50%aqueous methanol solution, whereby 9.0 parts of the following compound(12) were obtained. ##STR11##

After 18.4 parts of 4,4'-butylidenebis (6-t-butyl-m-cresol), 7.2 partsof potassium carbonate and 100 parts of sulfolane were stirred at 100°C. for 30 minutes, 9 parts of the compound (12) were added, followed bya reaction at 120° C. for 4 hours. The reaction mixture was poured into1000 parts of 50% aqueous methanol solution, and a precipitated solidwas collected by filtration and then dried. By column chromatographicpurification, 8.3 parts of the following compound (13) were obtained.##STR12##

Visible light absorption, λ_(max) : 596 nm εg: 1.9×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₆ H₅₆ N₂ O₄ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            78.86        8.00   4.00                                          Found (%)   78.82        8.05   4.11                                          ______________________________________                                    

In a vessel equipped with a stirrer and a nitrogen inlet tube, 36.8parts of 4,4'-bis(2-aminophenoxy)biphenyl and 202 parts ofN,N-dimethylformamide were charged. In a nitrogen atmosphere, 39.8 partsof 4,4'-(p-phenylenedioxy)diphthalic dianhydride were added in portionsat room temperature, followed by stirring for 20 hours. To the resultingpolyamic acid solution, 3.0 parts of the compound (13) were added andmixed. The solution so obtained was cast on a glass plate, followed byheat treatment at 200° C. for 5 hours. The filter so obtained had goodtransmittance characteristics and excellent heat resistance and moistureresistance. Its transmittance characteristics are shown in FIG. 3.

EXAMPLE 3

Ten parts of 1-amino-2,4-dibromoanthraquinone, 50 parts of 2,4-xylidineand 11.8 parts of sodium acetate were reacted at 130° C. for 5 hours.The reaction mixture was poured into 1000 parts of 50% aqueous methanolsolution, whereby 9.3 parts of the following compound (14) wereobtained. ##STR13##

After 18.4 parts of 4,4'-butylidenebis(6-t-butyl-m-cresol), 7.2 parts ofpotassium carbonate and 100 parts of sulfolane were stirred at 100° C.for 30 minutes, 9 parts of the compound (14) were added, followed by areaction at 120° C. for 4 hours. The reaction mixture was poured into1000 parts of 50% aqueous methanol solution, and a precipitated solidwas collected by filtration and then dried. By column chromatographicpurification, 8.0 parts of the following compound (15) were obtained.##STR14##

Visible light absorption, λ_(max) : 602 nm εg: 1.9×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₈ H₅₄ N₂ O₄ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            79.78        7.48   3.88                                          Found (%)   79.75        7.55   3.84                                          ______________________________________                                    

To 100 g of polystyrene, 1 g of the anthraquinone compound (15) wasadded. The resultant resin composition was injection molded so that afilter was fabricated. The filter had good durability and transmittancecharacteristics. Its transmittance spectrum is depicted in FIG. 4.

COMPARATIVE EXAMPLE 1

Using the dyestuff disclosed in Japanese Patent Laid-Open No.197459/1987, a filter was fabricated in a similar manner to Example 3.Characteristics of the filter were presented in Table 1, and atransmittance spectrum of the filter is depicted in FIG. 5.

COMPARATIVE EXAMPLE 2

Gelatin was colored with Acid Blue 90 to fabricate a filter.Characteristics of the gelatin filter are presented in Table 1, and atransmittance spectrum of the gelatin filer is depicted in FIG. 6.

Measuring methods of individual characteristics and the presentation ofthe measurement results were as follows.

1. Transmittance characteristics

When the transmittance was 10% or lower at (the wavelength for a maximumtransmittance ±80) nm and the maximum transmittance is 80% or higher: AWhen the transmittance was 10% or lower at (the wavelength for themaximum transmittance ±80) nm and the maximum transmittance is 70% orlower: B

2. Moisture resistance

In terms of a color difference ΔE in 100 hours at 80% humidity and 60°C.,

when ΔE≦3: A

when ΔE≧5: B

3. Light fastness

In terms of a color difference ΔE in 100 hours at 60° C. on afadeometer,

when ΔE≦3: A

when ΔE≧5: B

4. Heat resistance

In terms of a color difference ΔE in 1 hour at 250° C.,

when ΔE≦3: A

when ΔE≧5: B

                  TABLE 1                                                         ______________________________________                                        Transmittance  Moisture   Light    Heat                                       characteristics                                                                              resistance fastness resistance                                 ______________________________________                                        Ex. 1  A (FIG. 2)  A          A      A                                        Ex. 3  A (FIG. 4)  A          A      A                                        Comp..sup.1)                                                                         B (FIG. 5)  A          B      A                                        Ex. 1                                                                         Comp..sup.2)                                                                         A (FIG. 6)  B          B      B                                        Ex. 2                                                                         ______________________________________                                         .sup.1) Fabricated in a similar manner to Example 3 by using the dyestuff     (of the belowdescribed structural formula) of Japanese Patent Application     LaidOpen No. 197459/1987:                                                     ##STR15##                                                                    -  -                                                                           .sup.2) Filter obtained by coloring gelatin with the dyestuff, Acid Blue      90, disclosed on page 48 of "1990s Development and Market Trend of Specia     Functional Dyestuffs", CMC Co., Ltd.                                     

EXAMPLE 4

Ten parts of 1-amino-2,4-dibromoanthraquinone, 50 parts of ethanolamineand 11.8 parts of sodium acetate were reacted at 130° C. for 5 hours.The reaction mixture was poured into 1000 parts of 50% aqueous methanolsolution, whereby 9.0 parts of the following compound (16) wereobtained. ##STR16##

After 18.4 parts of 4,4'-butylidenebis(6-t-butyl-m-cresol), 7.2 parts ofpotassium carbonate and 100 parts of sulfolane were stirred at 100° C.for 30 minutes, 9 parts of the compound (16) were added, followed by areaction at 120° C. for 4 hours. The reaction mixture was poured into1000 parts of 50% aqueous methanol solution, and a precipitated solidwas collected by filtration and then dried. By column chromatographicpurification, 8.2 parts of the following compound (17) were obtained.##STR17##

Visible light absorption, λ_(max) : 595 nm εg: 2.1×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₂ H₅₀ N₂ O₅ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            76.13        7.55   4.23                                          Found (%)   76.02        7.59   4.22                                          ______________________________________                                    

To 100 g of polystyrene, 1 g of the anthraquinone compound (17) wasadded. The resultant resin composition was injection molded so that afilter was fabricated. The filter had good durability and transmittancecharacteristics.

EXAMPLE 5

Ten parts of 1-amino-2-bromo-4-hydroxyanthraquinone, 12 parts of4,4'-butylidenebis(6-tert-butyl-m-cresol) and 3.52 parts of potassiumhydroxide were reacted at 80° C. for 3 hours in 50 parts of sulfolane.The reaction mixture was poured into 500 parts of a 50% aqueous methanolsolution, whereby 8.9 parts of the following anthraquinone compound (18)were obtained. ##STR18##

Visible light absorption, λ_(max) : 515 nm εg: 2.4×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₀ H₄₅ NO₅ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            77.54        7.27   2.26                                          Found (%)   77.58        7.35   2.18                                          ______________________________________                                    

To 100 parts of polyvinyl chloride, 1 part of the compound (18) wasadded. The resultant resin composition was injection molded so that afilter was fabricated. The filter was good in both durability andtransmittance characteristics. Characteristics of the filter arepresented in Table 2, and the transmittance characteristics of thefilter are depicted in FIG. 7.

EXAMPLE 6

After 22.3 parts of 4,4'-butylidenebis(2-t-butylphenol), 4.8 parts ofpotassium carbonate and 100 parts of sulfolane were stirred at 80° C.for 30 minutes, 10 parts of 1-amino-2-bromo-4-hydroxyanthraquinone wereadded, followed by a reaction at 125° C. for further 6 hours. Thereaction mixture was poured into 1000 parts of ice water, and aprecipitated solid was collected by filtration and then dried. By columnchromatographic purification, 13 parts of the following compound (19)were obtained. ##STR19##

Visible light absorption, λ_(max) : 515 nm εg: 2.0×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₃₈ H₄₁ NO₅ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            81.57        7.33   2.50                                          Found (%)   81.45        7.41   2.45                                          ______________________________________                                    

One part of the anthraquinone compound (19) was dissolved in 25 parts ofthe below-described composition. Using a spinner, the resulting solutionwas spin-coated on a glass substrate. The resulting film was dried,pre-baked at 85°-100° C. for 2-5 minutes and through a mask having astripe-shaped pattern, exposed to light from a high-pressure mercurylamp (20-30 mj/cm², 2 minutes). The film so exposed was then developedto form a pattern. Finally, the film so patterned was post-baked at200°-230° C. for 10-30 minutes so that a red stripe filter was obtained.The thickness of the dyestuff layer was 2.2 μm. ##STR20##

The filter had good durability and transmittance characteristics. Itstransmittance characteristics are shown in FIG. 8.

COMPARATIVE EXAMPLE 3

Using the dyestuff of the below-described structural formula disclosedin Japanese Patent Laid-Open No. 108068/1987, a filter was fabricated ina similar manner to Example 6. Characteristics of the filter arepresented in Table 2, and transmittance characteristics of the filterare depicted in FIG. 9. In the filter so obtained, the dyestuff wasinsoluble in the binder polymer and precipitated in the form of a solid.##STR21##

                  TABLE 2                                                         ______________________________________                                        Transmittance Moisture  Light    Heat                                         characteristics                                                                             resistance                                                                              fastness resistance                                   ______________________________________                                        Ex. 5 A (FIG. 7)  A         A      A                                          Ex. 6 A (FIG. 8)  A         A      A                                          Comp..sup.1)                                                                        B (FIG. 9)  A         A      A                                          Ex. 3                                                                         ______________________________________                                         .sup.1) Fabricated in a similar manner to Example 6 by using the dyestuff     of Japanese Patent LaidOpen No. 108068/1987:                             

EXAMPLE 7

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (20),2.8 parts of 1,8-diazabicyclo 5.4.0!-7-undecene and 100 parts of n-amylalcohol: ##STR22## In a nitrogen atmosphere, the contents of the vesselwas heated to 110° C. At the same temperature, 0.6 part of cuprouschloride was next added, followed by a reaction at 110°-120° C. for 8hours. After completion of the reaction, the reaction mixture was cooledand insoluble matter was then removed by filtration. The filtrate wasconcentrated under reduced pressure to remove the solvent. By columnchromatographic purification, 9.2 parts of the following compound (21)and its isomers were obtained. ##STR23##

Visible light absorption, λ_(max) : 706 nm εg: 1.0×10⁵ ml/g.cm (solvent:toluene)

Elemental analysis for C₁₃₆ H₁₆₀ N₈ O₈ Cu:

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            77.88        7.64   5.34                                          Found (%)   77.77        7.80   5.31                                          ______________________________________                                    

In a vessel equipped with a stirrer and a nitrogen inlet tube, 36.8parts of 4,4'-bis(2-aminophenoxy)biphenyl and 202 parts ofN,N-dimethylformamide were charged. In a nitrogen atmosphere, 39.8 partsof 4,4'-(p-phenylenedioxy)diphthalic dianhydride were added in portionsat room temperature, followed by stirring for 20 hours. To the resultingpolyamic acid solution, 3.0 parts of the compound (21) were added andmixed. The solution so obtained was cast on a glass plate, followed byheat treatment at 200° C. for 5 hours. The filter so obtained had goodtransmittance characteristics and excellent heat resistance and moistureresistance. Its transmittance characteristics are shown in FIG. 10.

EXAMPLE 8

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (22),3.2 parts of 1,8-diazabicyclo 5.4.0!-7-undecene and 100 parts of n-amylalcohol: ##STR24## In a nitrogen atmosphere, the contents of the vesselwas heated to 110° C. At the same temperature, 1.1 parts of palladiumchloride were next added, followed by a reaction at 110°-120° C. for 8hours. After completion of the reaction, the reaction mixture was cooledand insoluble matter was then removed by filtration. The filtrate wasconcentrated under reduced pressure to remove the solvent. By columnchromatographic purification, 8.1 parts of the following compound (23)and its isomers were obtained. ##STR25##

Visible light absorption, λ_(max) : 703 nm εg: 1.1×10⁵ ml/g.cm (solvent:toluene)

Elemental analysis for C₁₂₈ H₁₄₄ N₈ O₈ Pd:

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            75.80        7.11   5.53                                          Found (%)   75.71        7.20   5.47                                          ______________________________________                                    

One part of the phthalocyanine (23) was dissolved in 25 parts of thebelow-described composition. Using a spinner, the resulting solution wasspin-coated on a glass substrate. The resulting film was dried, prebakedat 85°-100° C. for 2-5 minutes and through a mask having a stripe-shapedpattern, exposed to light from a high-pressure mercury lamp (20-30mj/cm², 2 minutes). The film so exposed was then developed to form apattern. Finally, the film so patterned was post-baked at 200°-230° C.for 10-30 minutes so that a stripe filter was obtained. The thickness ofthe dyestuff layer was 2 μm. ##STR26##

The filter had good durability and transmittance characteristics. Itstransmittance characteristics are shown in FIG. 11.

EXAMPLE 9

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (24),3.4 parts of 1,8-diazabicyclo 5.4.0!-7-undecene and 100 parts of n-amylalcohol: ##STR27## In a nitrogen atmosphere, the contents of the vesselwas heated to 110° C. At the same temperature, 0.7 part of cuprouschloride was next added, followed by a reaction at 110°-120° C. for 8hours. After completion of the reaction, the reaction mixture was cooledand insoluble matter was then removed by filtration. The filtrate wasconcentrated under reduced pressure to remove the solvent. By columnchromatographic purification, 10.3 parts of the following compound (25)and its isomers were obtained. ##STR28##

Visible light absorption, λ_(max) : 706 nm εg: 0.9×10⁵ ml/g.cm (solvent:toluene)

Elemental analysis for C₁₄₄ H₁₇₆ N₈ O₈ Cu:

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            78.28        7.97   5.80                                          Found (%)   78.30        8.05   5.74                                          ______________________________________                                    

To 100 g of polyvinyl chloride, 1 g of the compound (25) was added. Theresultant resin composition was injection molded so that a filter wasfabricated. The filter was good in both durability and transmittancecharacteristics.

EXAMPLE 10

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (26),3.5 parts of 1,8-diazabicyclo 5.4.0!-7-undecene and 100 parts of n-amylalcohol: ##STR29## In a nitrogen atmosphere, the contents of the vesselwas heated to 110° C. At the same temperature, 0.7 part of cuprouschloride was next added, followed by a reaction at 110°-120° C. for 8hours. After completion of the reaction, the reaction mixture was cooledand insoluble matter was then removed by filtration. The filtrate wasconcentrated under reduced pressure to remove the solvent. By columnchromatographic purification, 9.7 parts of the mixture of the followingcompound (27) and its isomers were obtained. ##STR30##

Visible light absorption, λ_(max) : 704 nm εg: 1.0×10⁵ ml/g.cm (solvent:toluene)

Elemental analysis for C₁₁₆ H₁₂₀ N₈ O₈ Cu:

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            76.67        6.61   6.17                                          Found (%)   76.61        6.72   6.20                                          ______________________________________                                    

To 100 g of polymethyl methacrylate, 1 g of the compound (27) was added.The resultant resin composition was injection molded so that a filterwas fabricated. The filter was good in both durability and transmittancecharacteristics.

EXAMPLE 11

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (28),15.5 parts of the below-described compound (29), 4.3 parts of potassiumcarbonate, 0.2 part of KI and 70 parts of N,N-dimethylformamide:##STR31## In a nitrogen atmosphere, the contents were reacted at 80° C.for 4 hours. After completion of the reaction, the reaction mixture waspoured into 1000 parts of ice water and a precipitated solid wascollected by filtration and then dried. By column chromatographicpurification, 12 parts of the following compound (30) were obtained.##STR32##

Visible light absorption, λ_(max) : 434 nm εg: 4.7×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₆ H₅₆ N₄ O₇ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            71.13        7.22   1.22                                          Found (%)   71.11        7.25   7.25                                          ______________________________________                                    

One part of the azo compound (30) was dissolved in 25 parts of thebelow-described composition. Using a spinner, the resulting solution wasspin-coated on a glass substrate. The resulting film was dried,pre-baked at 85°-100° C. for 2-5 minutes and through a mask having astripe-shaped pattern, exposed to light from a high-pressure mercurylamp (20-30 mj/cm², 2 minutes). The film so exposed was then developedto form a pattern. Finally, the film so patterned was post-baked at200°-230° C. for 10-30 minutes so that a stripe filter was obtained. Thethickness of the dyestuff layer was 2.1 μm. ##STR33##

The filter had good durability and transmittance characteristics.

EXAMPLE 12

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (31),15.0 parts of the above-described compound (29), 4.5 parts of potassiumcarbonate, 0.1 part of KI and 80 parts of N,N-dimethylformamide:##STR34## In a nitrogen atmosphere, the contents were reacted at 80° C.for 4 hours. After completion of the reaction, the reaction mixture waspoured into 1000 parts of ice water and a precipitated solid wascollected by filtration and then dried. By column chromatographicpurification, 11 parts of the following compound (32) were obtained.##STR35##

Visible light absorption, λ_(max) : 432 nm εg: 4.8×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₇ H₅₆ N₄ O₇ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            71.39        7.34   7.09                                          Found (%)   71.45        7.35   7.05                                          ______________________________________                                    

To 100 parts of polymethyl methacrylate, 1 part of the compound (32) wasadded. The resultant resin composition was injection molded so that afilter was fabricated. The filter was good in both durability andtransmittance characteristics.

EXAMPLE 13

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (33),9.9 parts of the below-described compound (34), 3.7 parts of potassiumcarbonate, 0.3 part of KI and 80 parts of N,N-dimethylformamide:##STR36## In a nitrogen atmosphere, the contents were reacted at 80° C.for 4 hours. After completion of the reaction, the reaction mixture waspoured into 1000 parts of ice water and a precipitated solid wascollected by filtration and then dried. By column chromatographicpurification, 11.2 parts of the following compound (35) were obtained.##STR37##

Visible light absorption, λ_(max) : 435 nm εg: 4.6×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₃ H₅₂ N₄ O₅ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            73.30        7.39   7.95                                          Found (%)   73.25        7.45   7.99                                          ______________________________________                                    

To 100 parts of polyvinyl chloride, 1 part of the compound (35) wasadded. The resultant resin composition was injection molded so that afilter was fabricated. The filter was good in both durability andtransmittance characteristics.

EXAMPLE 14

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (36),18.3 parts of the below-described compound (37), 4.5 parts of potassiumcarbonate, 0.2 part of KI and 100 parts of N,N-dimethylformamide:##STR38## In a nitrogen atmosphere, the contents were reacted at 80° C.for 5 hours. After completion of the reaction, the reaction mixture waspoured into 1000 parts of ice water and a precipitated solid wascollected by filtration and then dried. By column chromatographicpurification, 11.2 parts of the following compound (38) were obtained.##STR39##

Visible light absorption, λ_(max) : 450 nm εg: 5.5×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₅₀ H₅₅ NO₈ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            75.28        6.90   1.76                                          Found (%)   75.32        6.72   1.80                                          ______________________________________                                    

To 100 parts of polyvinyl chloride, 1 part of the compound (38) wasadded. The resultant resin composition was injection molded so that afilter was fabricated. The filter was good in both durability andtransmittance characteristics.

EXAMPLE 15

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the above-described compound (36),17.2 parts of the below-described compound (39), 4.4 parts of potassiumcarbonate, 0.2 part of KI and 80 parts of N,N-dimethylformamide:##STR40## In a nitrogen atmosphere, the contents were reacted at 80° C.for 4 hours. After completion of the reaction, the reaction mixture waspoured into 1000 parts of ice water and a precipitated solid wascollected by filtration and then dried. By column chromatographicpurification, 11 parts of the following compound (40) were obtained.##STR41##

Visible light absorption, λ_(max) : 451 nm εg: 5.4×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₈ H₅₁ NO₈ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            74.90        6.63   1.82                                          Found (%)   75.03        6.62   1.85                                          ______________________________________                                    

One part of the quinophthalone compound (40) was dissolved in 25 partsof the below-described composition. Using a spinner, the resultingsolution was spin-coated on a glass substrate. The resulting film wasdried, pre-baked at 85°-100° C. for 2-5 minutes and through a maskhaving a stripe-shaped pattern, exposed to light from a high-pressuremercury lamp (20-30 mj/cm², 2 minutes). The film so exposed was thendeveloped to form a pattern. Finally, the film so patterned waspost-baked at 200°-230° C. for 10-30 minutes so that a stripe filter wasobtained. The thickness of the dyestuff layer was 2 μm. ##STR42##

The filter had good durability and transmittance characteristics.

EXAMPLE 16

In a vessel equipped with a stirrer, reflux condenser and a nitrogeninlet tube, were charged 10 parts of the below-described compound (41),18.9 parts of the below-described compound (42), 4.6 parts of potassiumcarbonate, 0.3 part of KI and 80 parts of N,N-dimethylformamide:##STR43##

In a nitrogen atmosphere, the contents were reacted at 80° C. for 4hours. After completion of the reaction, the reaction mixture was pouredinto 1000 parts of ice water and a precipitated solid was collected byfiltration and then dried. By column chromatographic purification, 12.1parts of the following compound (43) were obtained. ##STR44##

Visible light absorption, λ_(max) : 448 nm εg: 5.2×10⁴ ml/g.cm (solvent:toluene)

Elemental analysis for C₄₉ H₅₃ NO₈ :

    ______________________________________                                                  C          H      N                                                 ______________________________________                                        Calculated (%)                                                                            75.10        6.77   1.79                                          Found (%)   75.15        6.72   1.82                                          ______________________________________                                    

To 100 parts of polymethyl methacrylate, 1 part of the compound (43) wasadded. The resultant resin composition was injection molded so that afilter was fabricated. The filter was good in both durability andtransmittance characteristics.

EXAMPLE 17-86

In each Example, the dyestuff represented by formula (1) in which R¹ toR¹⁰ are shown in Table 3 and the corresponding resin also shown in Table3 were used to fabricate a filter. The filter had good durability andfilter characteristics.

Incidentally, the resin abbreviations in Table 3 stand for thebelow-described resins. The reference of "Examples 6, 11 or 15" meansuse of the same resin composition as in Example 6, 11 or 15.

PS: Polystyrene

PMMA: Polymethyl methacrylate

PC: Polycarbonate

PET: Polyethylene terephthalate

PVC: Polyvinyl chloride

SD-17: Trade name, product of Dainippon Ink & Chemicals, Incorporated

    TABLE 3                                                                          - Ex-                                                                          am-                                                                            ple Dye X n R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7           R.sup.8 R.sup.9 R.sup.10 Resin                                                  17                                                                             ##STR45##                                                                      -- 1 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 SD-17                                                                       18                                                                        ##STR46##                                                                      -- 1 H H H H H H H H H i-C.sub.3                                               H.sub.7 SD-17                                                                                                  19                                             ##STR47##                                                                      -- 1 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 SD-17                                                                       20                                                                        ##STR48##                                                                      -- 1 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 SD-17                                                                       21                                                                        ##STR49##                                                                      -- 1 t-C.sub.4 H.sub.9 H H CH.sub.3 CH.sub.3 H H t-C.sub.4 H.sub.9 H          C.sub.3                                                                         H.sub.7 PMMA                                                                        22                                                                        ##STR50##                                                                      -- 1 t-C.sub.4 H.sub.9 H H i-C.sub.3 H.sub.7 H t-C.sub.4 H.sub.9              i-C.sub.3 H.sub.7 H H C.sub.4                                                   H.sub.9 PMMA                                                                                               23                                                 ##STR51##                                                                      -- 1 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 PET                                                                         24                                                                        ##STR52##                                                                      -- 1 CH.sub.3 H H i-C.sub.3 H.sub.7 CH.sub.3 H H i-C.sub.3 H.sub.7            CH.sub.3 C.sub.4                                                                H.sub.9 PMMA                                                                                  25                                                              ##STR53##                                                                      -- 1 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3       C.sub.5                                                                         H.sub.11 PC                                                                         26                                                                        ##STR54##                                                                      -- 1 i-C.sub.3 H.sub.7 H H H i-C.sub.3 H.sub.7 H H H i-C.sub.3 H.sub.7        H PS                                                                           27                                                                              ##STR55##                                                                      -- 1 i-C.sub.3 H.sub.7 H i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 H            i-C.sub.3 H.sub.7 i-C.sub.3                                                     H.sub.7 CH.sub.3 PET                                                                                     28                                                   ##STR56##                                                                      -- 1 i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 i-C.sub.3 H.sub.7 H H            i-C.sub.3 H.sub.7 i-C.sub.3 H.sub.7 C.sub.3                                     H.sub.7 PC                                                                                                               29                                   ##STR57##                                                                      -- 1 OCH.sub.3 H OCH.sub.3 H H OCH.sub.3 H OCH.sub.3 H                         ##STR58##                                                                      PVC                                                                           30                                                                              ##STR59##                                                                      -- 1 OCH.sub.3 H OCH.sub.3 H H OCH.sub.3 H OCH.sub.3 H                         ##STR60##                                                                      PET                                                                           31                                                                              ##STR61##                                                                      -- 1 OCH.sub.3 H H H H OCH.sub.3 H H H                                         ##STR62##                                                                      PC                                                                            32                                                                              ##STR63##                                                                      -- 1 Cl H H Cl Cl H H Cl CH.sub.3                                              ##STR64##                                                                      Example 6                                                                     33                                                                              ##STR65##                                                                      -- 1 Cl H Cl H H Cl H Cl CH.sub.3                                              ##STR66##                                                                      Example 6                                                                     34                                                                              ##STR67##                                                                      -- 1 OC.sub.2 H.sub.4 Cl H H H H OC.sub.2 H.sub.4 Cl H H H C.sub.4            H.sub.9 Example 6                                                              35                                                                              ##STR68##                                                                      -- 1 H H H t-C.sub.4 H.sub.9 H H t-C.sub.4 H.sub.9 H H C.sub.4 H.sub.9        Example 6                                                                      36                                                                              ##STR69##                                                                      -- 1 CH.sub.3 H H CH.sub.3 H CH.sub.3 CH.sub.3 H H C.sub.5 H.sub.11           Example 11                                                                     37                                                                              ##STR70##                                                                      -- 1 C.sub.2 H.sub.5 H C.sub.2 H.sub.5 H H C.sub.2 H.sub.5 H C.sub.2          H.sub.5 H i-C.sub.3                                                             H.sub.7 Example 11                                                                               38                                                           ##STR71##                                                                      -- 1 i-C.sub.3 H.sub.7 H H CH.sub.3 H i-C.sub.3 H.sub.7 CH.sub.3 H            C.sub.3                                                                         H.sub.7 CH.sub.3 Example 15                                                         39                                                                        ##STR72##                                                                      -- 1 OCH.sub.3 H H H H OCH.sub.3 H H C.sub.3 H.sub.7 H Example 15                                                                                40           ##STR73##                                                                      -- 1 OCH.sub.3 H OCH.sub.3 H H OCH.sub.3 H OCH.sub.3 C.sub.4 H.sub.9 H        Example 15                                                                     41                                                                              ##STR74##                                                                      -- 1 OCH.sub.3 H Br H H OCH.sub.3 H Br C.sub.4                                 H.sub.9 H PMMA                                                                                                               42                               ##STR75##                                                                      -- 1 CH.sub.3 H H Br H CH.sub.3 Br H CH(CH.sub.3).sub.2 H PVC                 43                                                                              ##STR76##                                                                      -- 1 CH.sub.3 CH.sub.3 Br H H Br CH.sub.3 CH.sub.3 CH(CH.sub.3).sub.2 H       PVC                                                                            44                                                                              ##STR77##                                                                      -- 1 i-C.sub.3 H.sub.7 H i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 H            i-C.sub.3 H.sub.7 CH.sub.2                                                      CH(CH.sub.3).sub.2 H PET                                                                                45                                                    ##STR78##                                                                      -- 1 Br H Br H H Br H Br C.sub.3                                               H.sub.7 H PS                                                                                                   46                                             ##STR79##                                                                      -- 1 i-C.sub.3 H.sub.7 H H CH.sub.3 H i-C.sub.3 H.sub.7 CH.sub.3 H            C.sub.4                                                                         H.sub.9 CH.sub.3 PET                                                                47                                                                        ##STR80##                                                                      -- 1 cyclo-C.sub.5 H.sub.11 H H H H cyclo-C.sub.5 H.sub.11 H H C.sub.7        H.sub.15 H PMMA                                                                48                                                                              ##STR81##                                                                      -- 1 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 PMMA                                                                        49                                                                        ##STR82##                                                                      -- 1 H H H H H H H H H i-C.sub.3                                               H.sub.7 PMMA                                                                                                   50                                             ##STR83##                                                                      -- 1 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 PMMA                                                                        51                                                                        ##STR84##                                                                      -- 1 t-C.sub.4 H.sub.9 H H i-C.sub.3 H.sub.7 H t-C.sub.4 H.sub.9              i-C.sub.3 H.sub.7 H H C.sub.5                                                   H.sub.11 PET                                                                                               52                                                 ##STR85##                                                                      -- 1 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H            CH.sub.3 C.sub.4                                                                H.sub.9 Example 11                                                                            53                                                              ##STR86##                                                                      -- 1 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.3       C.sub.5                                                                         H.sub.11 Example 11                                                                 54                                                                        ##STR87##                                                                      ##STR88##                                                                      1 i-C.sub.3 H.sub.7 H H H H i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 H         Example 11                                                                     55                                                                              ##STR89##                                                                      ##STR90##                                                                      1 i-C.sub.3 H.sub.7 H i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 H               i-C.sub.3 H.sub.7 i-C.sub.3                                                     H.sub.7 CH.sub.3 Example 11                                                                              56                                                   ##STR91##                                                                      ##STR92##                                                                      1 i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 i-C.sub.3 H.sub.7 H H               i-C.sub.3 H.sub.7 i-C.sub.3 H.sub.7 C.sub.3                                     H.sub.7 Example 6                                                                                                        57                                   ##STR93##                                                                      ##STR94##                                                                      1 OCH.sub.3 H OCH.sub.3 H H OCH.sub.3 H OCH.sub.3 H                            ##STR95##                                                                      Example 6                                                                     58                                                                              ##STR96##                                                                      ##STR97##                                                                      1 OCH.sub.3 H OCH.sub.3 H H OCH.sub.3 H OCH.sub.3 H                            ##STR98##                                                                      Example 6                                                                     59                                                                              ##STR99##                                                                      ##STR100##                                                                     1 OCH.sub.3 H H H H OCH.sub.3 H H H                                            ##STR101##                                                                     PMMA                                                                          60                                                                              ##STR102##                                                                     ##STR103##                                                                     1 Cl H H Cl Cl H H Cl CH.sub.3                                                 ##STR104##                                                                     PET                                                                           61                                                                              ##STR105##                                                                     ##STR106##                                                                     1 Cl H Cl H H Cl H Cl CH.sub.3                                                 ##STR107##                                                                     PC                                                                            62                                                                              ##STR108##                                                                     ##STR109##                                                                     1 OC.sub.2 H.sub.4 Cl H H H H OC.sub.2 H.sub.4 Cl H H H C.sub.4 H.sub.9       PVC                                                                            63                                                                              ##STR110##                                                                     ##STR111##                                                                     1 H H H t-C.sub.4 H.sub.9 H H t-C.sub.4 H.sub.9 H H C.sub.4 H.sub.9 PVC       64                                                                              ##STR112##                                                                     ##STR113##                                                                     1 CH.sub.3 H H CH.sub.3 CH.sub.3 H H CH.sub.3 H C.sub.5 H.sub.11 PVC                                                                                65        ##STR114##                                                                     ##STR115##                                                                     1 C.sub.2 H.sub.5 H C.sub.2 H.sub.5 H H C.sub.2 H.sub.5 H C.sub.2             H.sub.5 C.sub.2 H.sub.5 i-C.sub.3                                               H.sub.7 Example 15                                                                                             66                                             ##STR116##                                                                     ##STR117##                                                                     1 i-C.sub.3 H.sub.7 H H H H i-C.sub.3 H.sub.7 H H C.sub.3 H.sub.7             CH.sub.3 PET                                                                   67                                                                              ##STR118##                                                                     ##STR119##                                                                     1 OCH.sub.3 H H H H OCH.sub.3 H H C.sub.3                                      H.sub.7 H PMMA                                                                                                          68                                    ##STR120##                                                                     ##STR121##                                                                     1 OCH.sub.3 H OCH.sub.3 H H OCH.sub.3 H OCH.sub.3 C.sub.4 H.sub.9 H           Example 6                                                                      69                                                                              ##STR122##                                                                     ##STR123##                                                                     1 OCH.sub.3 H Br H H OCH.sub.3 H Br C.sub.4 H.sub.9 H Example 6                                                                                70             ##STR124##                                                                     ##STR125##                                                                     1 CH.sub.3 H Br H H CH.sub.3 H Br i-C.sub.3 H.sub.7 H Example 6                                                                                71             ##STR126##                                                                     -- 1 CH.sub.3 CH.sub.3 Br H CH.sub.3 CH.sub.3 H Br i-C.sub.3 H.sub.7 H        Example 11                                                                     72                                                                              ##STR127##                                                                     -- 1 i-C.sub.3 H.sub.7 H i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 H            i-C.sub.3                                                                       H.sub.7                                                                       ##STR128##                                                                      H Example 11                                                                  73                                                                              ##STR129##                                                                     -- 4 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 PMMA                                                                        74                                                                        ##STR130##                                                                     -- 4 H H H H H H H H H i-C.sub.3                                               H.sub.7 PET                                                                                                    75                                             ##STR131##                                                                     -- 4 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 PVC                                                                         76                                                                        ##STR132##                                                                     -- 4 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 PC                                                                          77                                                                        ##STR133##                                                                     -- 4 t-C.sub.4 H.sub.9 H H CH.sub.3 CH.sub.3 H H t-C.sub.4 H.sub.9 H          C.sub.3                                                                         H.sub.7 Example 11                                                                  78                                                                        ##STR134##                                                                     -- 4 t-C.sub.4 H.sub.9 H H i-C.sub.3 H.sub.7 H t-C.sub.4 H.sub.9              i-C.sub.3 H.sub.7 H H C.sub.4                                                   H.sub.9 Example 11                                                                                         79                                                 ##STR135##                                                                     -- 4 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H H          C.sub.4                                                                         H.sub.9 Example 11                                                                  80                                                                        ##STR136##                                                                     -- 4 CH.sub.3 H H i-C.sub.3 H.sub.7 H CH.sub.3 i-C.sub.3 H.sub.7 H            CH.sub.3 C.sub.4                                                                H.sub.9 Example 11                                                                            81                                                              ##STR137##                                                                     -- 8 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.3       i-C.sub.3                                                                       H.sub.7 Example 11                                                                    82                                                                      ##STR138##                                                                     -- 8 i-C.sub.3 H.sub.7 H H H H i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7        H PMMA                                                                         83                                                                              ##STR139##                                                                     -- 8 i-C.sub.3 H.sub.7 H i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 H            i-C.sub.3 H.sub.7 i-C.sub.3                                                     H.sub.7 CH.sub.3 PC                                                                                      84                                                   ##STR140##                                                                     ##STR141##                                                                     4 i-C.sub.3 H.sub.7 H H i-C.sub.3 H.sub.7 i-C.sub.3 H.sub.7 H H               i-C.sub.3 H.sub.7 i-C.sub.3 H.sub.7 C.sub.3                                     H.sub.7 PVC                                                                                                              85                                   ##STR142##                                                                     ##STR143##                                                                     4 OCH.sub.3 H OCH.sub.3 H H OCH.sub.3 H OCH.sub.3 H                            ##STR144##                                                                     PVC                                                                           86                                                                              ##STR145##                                                                     -- 10 CH.sub.3 H H CH.sub.3 H CH.sub.3 CH.sub.3 H H C.sub.5 H.sub.11          PMMA                                                                      

What is claimed is:
 1. A color filter comprising an opticallytransparent substrate and a dyestuff represented by the followingformula ( 5): ##STR146## wherein R¹ to R⁸ independently represent ahydrogen atom; a halogen atom; an unsubstituted alkyl group which islinear or branched and has 1 to 20 carbon atoms; an alkyl group which islinear or branched and is substituted by at least one of alkoxy,halogen, hydroxyl or amino substituents and has 1 to 30 carbon atoms intotal; an unsubstituted cycloalkyl group which has 5 to 12 carbon atoms;a cycloalkyl group which is substituted by at least one of halogen,alkyl or alkoxy substituents and has 5 to 20 carbon atoms in total; anunsubstituted alkoxy group which is linear or branched and has 1 to 10carbon atoms; or an alkoxy group which is linear or branched and issubstituted by at least one of alkoxy or halogen substituents and has 1to 20 carbon atoms in total; R⁹ and R¹⁰ independently represent ahydrogen atom; an unsubstituted alkyl group which is linear or branchedand has 1 to 20 carbon atoms; or an alkyl group which is linear orbranched and is substituted by at least one of alkoxy or halogensubstituents and has 1 to 30 carbon atoms in total with the provisionthat one of R⁹ and R¹⁰ has 3 or more carbon atoms; R¹⁴ and R¹⁵independently represent a hydrogen atom; an unsubstituted, linear orbranched alkyl group having 1 to 20 carbon atoms; a linear or branchedalkyl group substituted by at least one of halogen, alkoxy, hydroxyl oramino groups and having 1 to 30 carbon atoms in total; an unsubstituted,linear or branched alkoxy group having 1 to 20 carbon atoms; a linear orbranched alkoxy group substituted by at least one of halogen, alkoxy,hydroxyl or amino groups and having 1 to 20 carbon atoms in total; or ahalogen atom; and R¹⁶ represents a hydrogen atom or a halogen atom; andX represents --CO--, --COOCH2CO-- or --COOCH₂ CH₂ CO--.
 2. A colorfilter comprising an optically transparent substrate and a dyestuffrepresented by the following formula (6): ##STR147## wherein R¹ to R⁸independently represent a hydrogen atom; a halogen atom; anunsubstituted alkyl group which is linear or branched and has 1 to 20carbon atoms; an alkyl group which is linear or branched and issubstituted by at least one of alkoxy, halogen, hydroxyl or aminosubstituents and has 1 to 30 carbon atoms in total; an unsubstitutedcycloalkyl group which has 5 to 12 carbon atoms; a cycloalkyl groupwhich is substituted by at least one of halogen, alkyl or alkoxysubstituents and has 5 to 20 carbon atoms in total; an unsubstitutedalkoxy group which is linear or branched and has 1 to 10 carbon atoms;or an alkoxy group which is linear or branched and is substituted by atleast one of alkoxy or halogen substituents and has 1 to 20 carbon atomsin total; R⁹ and R¹⁰ independently represent a hydrogen atom; anunsubstituted alkyl group which is linear or branched and has 1 to 20carbon atoms; or an alkyl group which is linear or branched and issubstituted by at least one of alkoxy or halogen substituents and has 1to 30 carbon atoms in total with the provision that one of R⁹ and R¹⁰has 3 or more carbon atoms; R¹⁷ represents an unsubstituted, linear orbranched alkyl group having 1 to 20 carbon atoms; a linear or branchedalkyl group substituted by at least one of halogen, alkoxy, hydroxyl oramino groups and having 1 to 30 carbon atoms in total; and X represents--CO-- or --COOCH₂ CO--.